Crossdressing is often looked down upon and it is often greeted with a frown. However, being a crossdresser, I would say that it is a thrilling ride. I was bullied all through my adolescence for being ‘feminine’ and when I came out as bisexual, I faced innumerable backlashes and was subjected to humiliation. However, I was lucky enough to have a handful of friends by my side, whom I could not thank enough. I was raised by a single mother after I lost my father to a brain stroke when I was at a tender age.
However, my mom tried her best to make me not feel my dad’s absence. While I was growing up, people around me have been emotionally abusing me and I frequently had to listen to the phrase, ‘Man up’. But who sets the standards of masculinity? Anyway, I am more inclined to my feminine side and I am quite comfortable with it. I tried dating a guy once but it ended up in a pathetic heartbreak. Nonetheless, it has been three years and I have moved on, at least I think I did.
I met my girlfriend in a fashion event where she was the showstopper. I still do not know how I managed to woo someone as hot as her. Katherine and I have been seeing each other for a year now and we like to try out different activities in bed. She is an adventurous woman who loves to live life in her own terms. Exploring our limits in bed is something we are fond of. Honestly, it is healthy in a relationship. Thus, we are hardly ever bored of each other. Last night however was different. I mean it in a good way.
The experience I am going to share with you is hardly 23 hours old. Katherine and I thought of an innovative plan. We were seeing each other after a month; hence we decided to make it special by the act of cross dressing. Initially, I was not sure if I wanted to do it since I have always been insecure about my sexuality. She convinced me somehow and I found myself giving in to her fantasies. The previous day, she went shopping and brought a few clothes for me. There I was, before the mirror, in maid attire with cat ears.
She was delighted to see me in the black dress with white laces and fishnets. I was uncomfortable initially, but eventually it felt good. I had always wondered how I would look in a woman’s attire and I did look gorgeous in it. She was already in my favorite red lingerie when I entered the room. She always looked ravishing with her small waist and poised structure. She walked towards me and I noticed that she was holding a whip in her hand. I smiled since I had started to anticipate the events that were going to follow.
Katherine asked me to bend down on the table, I obeyed my mistress. She lifted my dress up and ran the whip all over my ass gently. She pulled the strings of my underwear, rather panties. She whipped my ass several times, making me moan in pleasure. She stated that she was going to punish me the entire night for disobeying her. I enjoyed getting my ass whipped and spanked. She grabbed my hair and made me suffocate between her huge tits before making me go down on her. I spread her legs and ate her out for several minutes until her pussy was dripping wet.
She pushed me against the wall, pulled my panties down and inserted her strap on in my ass. It caught me off guard but I would admit that I had begun to like it. The hard and elongated thing felt amazing in my ass and I could feel my dick throbbing. She used it well on me and thrusted deeper and harder until I moaned her name. She kept fucking me in my ass, spanking it harder than ever. I could not get enough of it. She removed her bra and I could see her boobs bouncing while she shoved it deep inside me.
Finally, she went down on me. She knelt down, my legs still shaking. She lifted my dress up and pulled the panties down. My erect cock was in her mouth. Katherine licked it until it was wet enough and shoved it into her mouth. She caressed my thighs and canoodled with my dick. I was way too turned on to complain. She choked and gagged on it, spitting on it. She stroked it well and kept sucking on it. She wanted me to cum in her mouth. I abided by my mistress’s command and came in her mouth while she swallowed my cum and licked my dick dry.
This was my little experience I thought of sharing with you. So, yeah, crossdressing does not seem that bad after all, does it?
